Vat dyes of the anthraquinone series.



WILHEIJM HER-ZBERG AND WALTER BRUCK, OF SCI-IGNEBERG, NEAR BERLIN, GER-MANY, ASSIGNORS T0 Ao'rIEN GnsnLLsoHAr'r Fun- ANILIN FABRIKATIQN', or

BERLIN, GERMANY.

VAT DYES OF THE ANTHRA QUINONE SERIES.

mosses.-

No Drawing.

To all whom it may concern: 5

Be it known that we, VVILHELM Hnnznnno and lVAL'rnR BRUOK, subjects ofthe Emperor of Germany, residing at Schineberg,

-'ne'ar Berlin, Germany,-our post-oflice advaluable vat dyes of theant-hraquinone series are obtained by brominating a socalledanthraquinone acridgne which dones on their part can be obtained by theaction of a dehydrating agent upon anorthocarboxyphenylainino-anthraquinone, obtaining thus for instanceabody of the following formula: I

. if starting from alpha-chloroanthraquinone ceedby one of the methodsusual for this purpose; for instance, the parent material may be mixedwith a suitable solvent, such as nitrobenzene, and acted upon withbromin while heating. The new dyes thus obtained produce on cotton froma vat containing a hydrosulfite and an alkali red to bluish'r'ed to bluetints which are clear and intense and possess a very good fastness.

The process relating to thepresentinvention may also be carried out inthe presence of asubstance possessing a catalytic func tion, such as forinstance iodin or the like.

The following example serves to illus trate our invention, the partsbeing by weight: 326 parts of alpha-beta-authraquinone acridone (comparethe above given formula) are dissolved in about 3300 parts ofnitrobenzene while heating to about 150 0.; then while stirring 160parts of bromin are added drop by-drop. The reaction occurs with aconstant evolution of hydrobromic'acid; all the bromin having beeninfipecification of Lettersjatent. Application filed December. 30. 1910.

the manner in which it rnav Patented. Nov. 34,1911.

Serial No. 600,111.

troduced the temperature 'is' gradually raised up to 200 C. in ordertoquicklyeliminate 4 the rest of hydrobrom ic acid. On cooling thebromanthraquinone acridone separates in the shape of hrilliantcopper-redsmall crystals. The new product thus obtained, if pulverized, forms ablue-red powder, which is nearly insoluble in alcohol and benzene; it isdifiicultly soluble in nitrobenzene, anilin and pyridin. In concentratedsulfuric acid it dissolves to an orange-yellow solution, which on theaddition of ice separate bluered' flakes. The product gives ,withlifvdrosulfite and an alkali af'violet rat from which.

is obtained on cotton an intense and clear red tint which possesses avery good fast: ness.

Our presentinvention is not limited to the foregoing example or to thedetails given therein. Thus, for instance, instead of a. monobromoderivative there can also be obtained dibromo compounds of "ananthraquinone acridone. Furthermore derivatives of the simplestanthraquinone acridone used in the above example may be employed, suchas for instance alpha-methylalpha-beta-anthraquinone' acridone ordialpha-beta-anthraquinone diacridone or the like. On the other side onecan also pro-- ceed as follows: The parent material is dissolved inconcentrated sulfuric acid, this is made by draining, which paste isthen di rectly acted upon with bromin.

It is convenientto'state that there is also another way to obtain thenew.products of our present invention. This way starts from a bromoderivative of anthranilic acid; this is condensed with a halogenanthraquinone to the corresponding anthraquinonylamino compound, whichlatter by the action of a dehydrating agent is transformed into thedesired bromo-anthraquinone acridone.

Having now described our invention and be performed what we claim is,-

1. As new vat dyestufi's the halogenated anthraquinone acridones whichcontain the halogen substituted in the benzene nuclei,

which dyestuffs are insoluble in alcohol andv benzene, ditlicult-lysoluble in nitrobenzene, soluble in concentrated sulfuric acid to ayellowish solution, and which dye cotton from the vat red to blueshades.

2 As new vat dyestufis the halogenated anthraquinone acridones of thefollowing which contain the halogen substituted in the benzene nuclei,which dyestuffs are insoluble in alcohol and benzene, difiicultlysoluble in nitrobenzene, soluble in Concentrated sulfuric acid to ayellowish solution, and which dye cotton from the vet red to blueshades.

3LAs new vat dyestuii's the brominatecl enthi'aqu noneacnclones whichcontain the 'brornin substituted in the benzene nuclei which (lyestufisare insoluble in alcohol and 4. As a new vat dye thebrominateclalphabeta-anth'raquinone acrid'onawhich contains the brominin the benzene nucleus and which may be obtained by acting onalpha-betaanthraquinoneacridone, dissolved in nitrobenzene, with bromin,this new dye it pul verizecl forming a blue-red powder which produces oncotton from a vat containing a hydrosulfite and an alkali an intense andclear red tint possessing a very good fast ness, this new product beingnearly insoluble in alcohol and, benzene and oliflicultly soluble innitrobenzene, anilin and pyridin to a blue-red solution, and which newdye lissolves in concentrated sulfu 'ic acid to an orange-yellowsolution which on the addie. tion of ice separates blue-red flakes.

v In testimony whereot we have hereunto set our hands in presence of twosubscribing witnesses.

VYTII4IXEIJDVK HERZBERGi NA LTER BRUCK. Witnesses WOLDEMAR HAUPT, HENRYHAsPnR.

